EP0222425A3 - Brain-specific drug delivery - Google Patents

Brain-specific drug delivery

Info

Publication number
EP0222425A3
EP0222425A3 EP86201714A EP86201714A EP0222425A3 EP 0222425 A3 EP0222425 A3 EP 0222425A3 EP 86201714 A EP86201714 A EP 86201714A EP 86201714 A EP86201714 A EP 86201714A EP 0222425 A3 EP0222425 A3 EP 0222425A3
Authority
EP
European Patent Office
Prior art keywords
brain
ring
dihydropyridine
centrally acting
acting drug
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP86201714A
Other languages
German (de)
French (fr)
Other versions
EP0222425A2 (en
Inventor
Nicholas S. Bodor
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Florida
Original Assignee
University of Florida
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US06/379,316 external-priority patent/US4479932A/en
Priority claimed from US06/475,493 external-priority patent/US4622218A/en
Application filed by University of Florida filed Critical University of Florida
Publication of EP0222425A2 publication Critical patent/EP0222425A2/en
Publication of EP0222425A3 publication Critical patent/EP0222425A3/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/559—Redox delivery systems, e.g. dihydropyridine pyridinium salt redox systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
    • C07K14/70—Enkephalins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Zoology (AREA)
  • Toxicology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention provides compounds adapted for the site-­ specific/sustained delivery of a centrally acting drug species to the brain having the formula [D-DHC] and the non-toxic pharmaceutically acceptable salts thereof, wherein [D] is a centrally acting drug species containing at least one reactive -OH, -COOH, -SH, -NH- or -NH₂ functional group and [DHC] is the reduced, biooxidizable, blood-brain barrier penetrating lipoidal form of a dihydropyridine = pyridinium salt redox carrier comprising a dihydropyridine ring of the formula
EP86201714A 1982-05-18 1983-05-12 Brain-specific drug delivery Withdrawn EP0222425A3 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US379316 1982-05-18
US06/379,316 US4479932A (en) 1982-05-18 1982-05-18 Brain-specific drug delivery
US46154383A 1983-01-27 1983-01-27
US461543 1983-01-27
US475493 1983-03-15
US06/475,493 US4622218A (en) 1982-05-18 1983-03-15 Testicular-specific drug delivery

Related Parent Applications (2)

Application Number Title Priority Date Filing Date
EP83902034.4 Division 1983-05-12
EP83902034A Division EP0110955B1 (en) 1982-05-18 1983-05-12 Brain-specific drug delivery

Publications (2)

Publication Number Publication Date
EP0222425A2 EP0222425A2 (en) 1987-05-20
EP0222425A3 true EP0222425A3 (en) 1988-09-21

Family

ID=27409446

Family Applications (6)

Application Number Title Priority Date Filing Date
EP86201713A Withdrawn EP0224283A3 (en) 1982-05-18 1983-05-12 Brain-specific drug delivery
EP87201385A Withdrawn EP0256577A3 (en) 1982-05-18 1983-05-12 Brain-specific drug delivery
EP86201711A Withdrawn EP0221588A3 (en) 1982-05-18 1983-05-12 Brain-specific drug delivery
EP83902034A Expired - Lifetime EP0110955B1 (en) 1982-05-18 1983-05-12 Brain-specific drug delivery
EP86201714A Withdrawn EP0222425A3 (en) 1982-05-18 1983-05-12 Brain-specific drug delivery
EP87201384A Withdrawn EP0262696A3 (en) 1982-05-18 1983-05-12 Brain-specific drug delivery

Family Applications Before (4)

Application Number Title Priority Date Filing Date
EP86201713A Withdrawn EP0224283A3 (en) 1982-05-18 1983-05-12 Brain-specific drug delivery
EP87201385A Withdrawn EP0256577A3 (en) 1982-05-18 1983-05-12 Brain-specific drug delivery
EP86201711A Withdrawn EP0221588A3 (en) 1982-05-18 1983-05-12 Brain-specific drug delivery
EP83902034A Expired - Lifetime EP0110955B1 (en) 1982-05-18 1983-05-12 Brain-specific drug delivery

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP87201384A Withdrawn EP0262696A3 (en) 1982-05-18 1983-05-12 Brain-specific drug delivery

Country Status (9)

Country Link
EP (6) EP0224283A3 (en)
AT (1) ATE126695T1 (en)
AU (1) AU567433B2 (en)
CA (2) CA1253856A (en)
DE (1) DE3382795T2 (en)
ES (1) ES8502087A1 (en)
IE (1) IE69557B1 (en)
IT (1) IT1171851B (en)
WO (1) WO1983003968A1 (en)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3574869D1 (en) * 1984-02-29 1990-01-25 Univ Florida BRAIN-SPECIFIC ANALOGS OF CENTRALLY EFFECTIVE AMINES.
US4771059A (en) * 1984-02-29 1988-09-13 University Of Florida Brain-specific analogues of centrally acting amines
US4933438A (en) * 1984-02-29 1990-06-12 University Of Florida Brain-specific analogues of centrally acting amines
US5082853A (en) * 1984-02-29 1992-01-21 Bodor Nicholas S Brain-specific analogues of centrally acting amines
AU4635885A (en) * 1984-07-19 1986-02-25 University Of Florida Compounds for site-enhanced delivery of radionuclides and uses thereof
US4963688A (en) * 1984-07-19 1990-10-16 University Of Florida Compounds for site-enhanced delivery of radionuclides and uses thereof
AU4632085A (en) * 1984-07-19 1986-02-25 University Of Florida Novel radiopharmaceuticals and chelating agents useful in their preparation
US4764598A (en) * 1985-08-22 1988-08-16 The United States Of America As Represented By The Department Of Energy Precursors to radiopharmaceutical agents for tissue imaging
US4863911A (en) * 1986-08-04 1989-09-05 University Of Florida Method for treating male sexual dysfunction
US4888427A (en) * 1987-04-07 1989-12-19 University Of Florida Amino acids containing dihydropyridine ring systems for site-specific delivery of peptides to the brain
US5079366A (en) * 1987-04-07 1992-01-07 University Of Florida Quarternary pyridinium salts
US5017566A (en) * 1987-12-30 1991-05-21 University Of Florida Redox systems for brain-targeted drug delivery
US5002935A (en) * 1987-12-30 1991-03-26 University Of Florida Improvements in redox systems for brain-targeted drug delivery
EP0386644B1 (en) * 1989-03-10 1997-06-04 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Reagents for the determination of drugs
IL106998A0 (en) * 1992-09-17 1993-12-28 Univ Florida Brain-enhanced delivery of neuroactive peptides by sequential metabolism
KR101301577B1 (en) * 2010-08-20 2013-08-29 주식회사 바이오에프디엔씨 Nicotinoyl Peptide Derivatives and Cosmetic Composition Comprising the Same
CN104136431B (en) 2011-12-21 2017-03-15 小野药品工业株式会社 Pyridone and pyrimidone derivatives as plasma thromboplastin antecedent a inhibitor
CN109153639B (en) * 2016-03-14 2022-07-29 斯法尔制药私人有限公司 Trigonelline compounds
WO2018054721A1 (en) 2016-09-26 2018-03-29 Basf Se Pyridine compounds for controlling phytopathogenic harmful fungi
WO2018054723A1 (en) 2016-09-26 2018-03-29 Basf Se Pyridine compounds for controlling phytopathogenic harmful fungi
WO2018054711A1 (en) 2016-09-26 2018-03-29 Basf Se Pyridine compounds for controlling phytopathogenic harmful fungi
WO2018065182A1 (en) 2016-10-04 2018-04-12 Basf Se Reduced quinoline compounds as antifuni agents
WO2018073110A1 (en) 2016-10-20 2018-04-26 Basf Se Quinoline compounds as fungicides
WO2018134127A1 (en) 2017-01-23 2018-07-26 Basf Se Fungicidal pyridine compounds
CN110475772A (en) 2017-04-06 2019-11-19 巴斯夫欧洲公司 pyridine compound

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3929813A (en) 1973-12-26 1975-12-30 Interx Research Corp Novel pro-drug derivatives of pyridinium aldoxime type cholinesterase reactivators and process for preparing same
US3962447A (en) 1973-12-26 1976-06-08 Interx Research Corporation Novel pro-drug derivatives of pyridinium aldoxime type cholinesterase reactivators and method of using same
US4069322A (en) * 1976-10-12 1978-01-17 Interx Research Corporation Pro-drugs for the improved delivery of certain selected anti-inflammatory steroids
US4206220A (en) * 1978-07-13 1980-06-03 Interx Research Corporation Prodrugs for the improved delivery of non-steroidal anti-inflammatory agents

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
B. ROCHE: "Design of biopharmaceutical properties through prodrugs and analogs", 1977, pages 98-135, American Pharmaceutical Association, (N. BODOR) *
CHEMICAL AND ENGINEERING NEWS, 21st December 1981, pages 24,25, Washington D.C., US; R. RAWLS: "New methods let drugs past blood-brain barrier" *
JOURNAL OF MEDICINAL CHEMISTRY, vol. 26, April 1983, pages 313-318, Columbus, Ohio, US; N. BODOR et al.: "Improved delivery trough biological membranes. 11. A redox chemical drug-delivery system and its use for brain-specific delivery of phenylethylamine" *
JOURNAL OF MEDICINAL CHEMISTRY, vol. 26, April 1983, pages 528-534, Columbus, Ohio, US; N. BODOR: "Improved delivery through biological membranes. 13. Brain specific delivery of dopamine with a dihydropyridine pyridinium salt redox type delivery system" *
JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 67, no. 5, May 1978, pages 685-687, Washington, D.C. US; N. BODOR et al.: "Elimination of a quaternary pyridinium salt, delivered as its dihydropyridine derivative from brain of mice" *
R.L. JULIANO: "Drug delivery systems", 1980, pages 112-176, Oxford University Press, (V. STELLA et al.) *
SCIENCE, vol. 214, 18th December 1981, pages 1370-1372; N. BODOR et al.: "Site-specific, sustained release of drugs to the brain" *
T. HUGUCHI et al.: "Pro-drugs as novel drug delivery systems", 1975, pages 83-85, American Chemical Society, Washington D.C., US; (V. STELLA) *

Also Published As

Publication number Publication date
ES522489A0 (en) 1984-12-16
IE931149L (en) 1983-11-18
DE3382795D1 (en) 1995-09-28
EP0110955B1 (en) 1995-08-23
EP0256577A3 (en) 1988-07-06
EP0222425A2 (en) 1987-05-20
CA1253856A (en) 1989-05-09
ATE126695T1 (en) 1995-09-15
CA1327566C (en) 1994-03-08
IE831149L (en) 1983-11-18
ES8502087A1 (en) 1984-12-16
DE3382795T2 (en) 1996-02-15
EP0221588A2 (en) 1987-05-13
WO1983003968A1 (en) 1983-11-24
IE69557B1 (en) 1996-10-02
IT8348327A0 (en) 1983-05-18
EP0221588A3 (en) 1988-09-21
EP0262696A3 (en) 1988-07-20
EP0262696A2 (en) 1988-04-06
AU567433B2 (en) 1987-11-19
AU1703483A (en) 1983-12-02
EP0256577A2 (en) 1988-02-24
EP0224283A2 (en) 1987-06-03
EP0110955A1 (en) 1984-06-20
IT1171851B (en) 1987-06-10
EP0224283A3 (en) 1988-09-21

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Inventor name: BODOR, NICHOLAS S.